# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound-3
_database_code_depnum_ccdc_archive 'CCDC 1828493'
loop_
_audit_author_name
_audit_author_address
'DURGA PRASAD KAROTHU' 'NEW YORK UNIVERSITY ABU DHABI'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 B O3'
_chemical_formula_sum            'C15 H15 B O3'
_chemical_formula_weight         254.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x+, -y-1/2, z-1/2'

_cell_length_a                   24.529(2)
_cell_length_b                   4.5725(4)
_cell_length_c                   12.2240(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.256(3)
_cell_angle_gamma                90
_cell_volume                     1334.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0731 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8244.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17045
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.559
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2255
_reflns_number_total             2343
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.332
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.6480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1537
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C8(H8), C9(H9), C5(H5), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.31035(8) 0.5306(5) 0.70387(17) 0.0193(5) Uani 1 1 d . . . . .
O1 O 0.35869(9) 0.4627(5) 0.88644(17) 0.0197(5) Uani 1 1 d . . . . .
O3 O 0.14513(9) -0.1922(6) 0.64776(18) 0.0250(5) Uani 1 1 d . . . . .
C7 C 0.26716(12) 0.1637(7) 0.8210(3) 0.0184(7) Uani 1 1 d . . . . .
C12 C 0.22440(12) 0.0779(7) 0.7310(3) 0.0185(7) Uani 1 1 d . . . . .
H12 H 0.2231 0.1564 0.6584 0.022 Uiso 1 1 calc R . . . .
C11 C 0.18383(12) -0.1186(7) 0.7447(3) 0.0193(7) Uani 1 1 d . . . . .
C1 C 0.35745(13) 0.7044(7) 0.7261(3) 0.0184(7) Uani 1 1 d . . . . .
C6 C 0.38669(13) 0.6672(7) 0.8361(3) 0.0186(7) Uani 1 1 d . . . . .
C10 C 0.18506(13) -0.2335(8) 0.8512(3) 0.0223(7) Uani 1 1 d . . . . .
H10 H 0.1574 -0.3693 0.8616 0.027 Uiso 1 1 calc R . . . .
C8 C 0.26826(13) 0.0484(8) 0.9275(3) 0.0209(7) Uani 1 1 d . . . . .
H8 H 0.2971 0.1041 0.9901 0.025 Uiso 1 1 calc R . . . .
C9 C 0.22736(13) -0.1465(8) 0.9417(3) 0.0233(7) Uani 1 1 d . . . . .
H9 H 0.2282 -0.2222 1.0144 0.028 Uiso 1 1 calc R . . . .
C13 C 0.10312(13) -0.4081(8) 0.6518(3) 0.0251(8) Uani 1 1 d . . . . .
H13 H 0.1201 -0.5729 0.7020 0.030 Uiso 1 1 calc R . . . .
C5 C 0.43563(13) 0.8129(8) 0.8808(3) 0.0245(7) Uani 1 1 d . . . . .
H5 H 0.4557 0.7830 0.9562 0.029 Uiso 1 1 calc R . . . .
C2 C 0.37535(13) 0.8968(8) 0.6544(3) 0.0233(7) Uani 1 1 d . . . . .
H2 H 0.3551 0.9248 0.5790 0.028 Uiso 1 1 calc R . . . .
C3 C 0.42489(14) 1.0472(8) 0.6989(3) 0.0256(8) Uani 1 1 d . . . . .
H3 H 0.4390 1.1806 0.6526 0.031 Uiso 1 1 calc R . . . .
C4 C 0.45420(14) 1.0070(8) 0.8094(3) 0.0263(8) Uani 1 1 d . . . . .
H4 H 0.4877 1.1144 0.8368 0.032 Uiso 1 1 calc R . . . .
C14 C 0.05548(14) -0.2736(10) 0.6946(3) 0.0343(9) Uani 1 1 d . . . . .
H14A H 0.0702 -0.1881 0.7690 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.0279 -0.4251 0.6999 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.0375 -0.1206 0.6425 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.08399(15) -0.5171(9) 0.5320(3) 0.0330(9) Uani 1 1 d . . . . .
H15A H 0.0689 -0.3533 0.4826 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.0548 -0.6657 0.5283 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.1159 -0.6029 0.5076 0.050 Uiso 1 1 calc GR . . . .
B1 B 0.31194(14) 0.3852(8) 0.8039(3) 0.0175(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.377(4) . ?
O2 B1 1.385(4) . ?
O1 C6 1.385(4) . ?
O1 B1 1.389(4) . ?
O3 C11 1.379(4) . ?
O3 C13 1.436(4) . ?
C7 C12 1.391(4) . ?
C7 C8 1.400(4) . ?
C7 B1 1.543(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.380(4) . ?
C11 C10 1.398(4) . ?
C1 C6 1.382(4) . ?
C1 C2 1.383(5) . ?
C6 C5 1.372(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(5) . ?
C9 H9 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.516(5) . ?
C13 C15 1.516(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.393(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(5) . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 B1 104.5(2) . . ?
C6 O1 B1 105.1(2) . . ?
C11 O3 C13 119.7(2) . . ?
C12 C7 C8 118.7(3) . . ?
C12 C7 B1 120.6(3) . . ?
C8 C7 B1 120.7(3) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
O3 C11 C12 115.3(3) . . ?
O3 C11 C10 124.9(3) . . ?
C12 C11 C10 119.8(3) . . ?
O2 C1 C6 110.2(3) . . ?
O2 C1 C2 128.0(3) . . ?
C6 C1 C2 121.7(3) . . ?
C1 C6 O1 108.4(3) . . ?
C5 C6 O1 129.0(3) . . ?
C5 C6 C1 122.6(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.5 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
O3 C13 H13 109.8 . . ?
O3 C13 C14 110.4(3) . . ?
O3 C13 C15 105.0(3) . . ?
C14 C13 H13 109.8 . . ?
C14 C13 C15 112.0(3) . . ?
C15 C13 H13 109.8 . . ?
C6 C5 H5 121.9 . . ?
C6 C5 C4 116.2(3) . . ?
C4 C5 H5 121.9 . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.2(3) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 B1 O1 111.7(3) . . ?
O2 B1 C7 123.9(3) . . ?
O1 B1 C7 124.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C6 O1 0.8(3) . . . . ?
O2 C1 C6 C5 179.6(3) . . . . ?
O2 C1 C2 C3 179.8(3) . . . . ?
O1 C6 C5 C4 179.7(3) . . . . ?
O3 C11 C10 C9 178.3(3) . . . . ?
C7 C12 C11 O3 -177.8(3) . . . . ?
C7 C12 C11 C10 0.5(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C12 C7 C8 C9 0.0(5) . . . . ?
C12 C7 B1 O2 5.9(5) . . . . ?
C12 C7 B1 O1 -173.9(3) . . . . ?
C12 C11 C10 C9 0.1(5) . . . . ?
C11 O3 C13 C14 80.4(4) . . . . ?
C11 O3 C13 C15 -158.7(3) . . . . ?
C11 C10 C9 C8 -0.7(5) . . . . ?
C1 O2 B1 O1 -0.4(3) . . . . ?
C1 O2 B1 C7 179.7(3) . . . . ?
C1 C6 C5 C4 1.1(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C6 O1 B1 O2 0.9(3) . . . . ?
C6 O1 B1 C7 -179.3(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C6 C5 C4 C3 -0.7(5) . . . . ?
C8 C7 C12 C11 -0.6(5) . . . . ?
C8 C7 B1 O2 -173.2(3) . . . . ?
C8 C7 B1 O1 7.0(5) . . . . ?
C13 O3 C11 C12 176.4(3) . . . . ?
C13 O3 C11 C10 -1.9(5) . . . . ?
C2 C1 C6 O1 179.9(3) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
B1 O2 C1 C6 -0.2(3) . . . . ?
B1 O2 C1 C2 -179.2(3) . . . . ?
B1 O1 C6 C1 -1.0(3) . . . . ?
B1 O1 C6 C5 -179.7(3) . . . . ?
B1 C7 C12 C11 -179.6(3) . . . . ?
B1 C7 C8 C9 179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
